Jobs › Companies › CNA › Senior AI Software Engineer

About this Senior AI Software Engineer role at CNA

CNA · Onsite · Chicago, IL, USA

You have a clear vision of where your career can go. And we have the leadership to help you get there. At CNA, we strive to create a culture in which people know they matter and are part of something important, ensuring the abilities of all employees are used to their fullest potential. 

Individual contributor responsible for designing, building, and operationalizing AI-driven solutions that integrate seamlessly into enterprise systems. This role combines hands-on engineering, architecture, and governance, ensuring AI solutions are scalable, secure, compliant, and aligned with business objectives.

JOB DESCRIPTION:

Essential Duties & Responsibilities

  • Performs a combination of duties in accordance with departmental guidelines:
  • Design and build enterprise AI applications using LLMs, prompt workflows, RAG, and agent-based patterns
  • Evaluate model quality, latency, cost, safety, and business effectiveness
  • Implement responsible AI controls, observability, and governance for production AI systems
  • Partner with architects, product owners, and business teams to identify and scale high-value AI use cases
  • Convert prototypes into production-ready, reliable applications
  • Enable automation of repeatable business processes using AI
  • Develop APIs and microservices to expose AI capabilities
  • Integrate AI solutions with enterprise platforms (claims, document systems, data platforms)
  • Ensure scalability, resiliency, and cost optimization
  • Implement test automation (unit, integration, end-to-end)
  • Apply secure coding practices (OAuth, JWT, secrets management)
  • Mentor engineers and guide AI best practices
  • Collaborate with business units, IT, and vendors
  • Evaluate emerging AI technologies and recommend solutions

May perform additional duties as assigned.

Reporting Relationship

  • Typically, Director or above

Skills, Knowledge & Abilities

  • Strong programming skills in Java, Python, TypeScript, FastAPI, Spring Boot for APIs and services.
  • Experience using AI-enabled development tools such as GitHub Copilot, Claude Code, Cursor, and MCPs.
  • Experience with RAG (Retrieval-Augmented Generation) pipeline architecture and development.
  • Experience with agentic system design for multi-step automation (single-agent and multi-agent), including orchestration, state and memory patterns, tool integration, and safe autonomy controls (permissions, approvals, and auditability).
  • Experience with Google Cloud Platform (GCP), including services such as GKE, Cloud Storage, PostgreSQL, Pub/Sub, Secret Manager, BigQuery, and Vertex AI.
  • Advanced knowledge of designing and building integration platforms, APIs, and web services.
  • Experience with CI/CD automation using tools such as Docker, GKE, GitHub, and GitHub Actions.
  • Strong analytical, problem-solving, and communication skills
  • Experience with SQL/NoSQL data stores (modeling and query optimization)
  • Automated testing experience (unit and integration)
  • Working knowledge of React and front-end fundamentals (components, state, and API integration)
  • Strong understanding of SRE and observability fundamentals (logs, metrics, traces) and how to use them to diagnose distributed system behavior
  • In-depth knowledge of the system development life cycle and of system and application development technology alternatives.
  • Experience working in high-performing Agile teams
  • Excellent communication and interpersonal skills, with the ability to work effectively with peers, IT management and staff, and internal and external business partners and clients.
  • Preferred insurance industry knowledge.

Education & Experience

  • Bachelor’s degree in computer science or related discipline, or equivalent work experience.
  • Typically, a minimum of 7 years of systems analysis and application development experience, including 3+ years of experience building AI solutions.
  • Applicable certifications preferred.


LI-Hybrid

In certain jurisdictions, CNA is legally required to include a reasonable estimate of the compensation for this role. In District of Columbia, California, Colorado, Connecticut, Illinois, Maryland, Massachusetts, New York and Washington, the national base pay range for this job level is $72,000 to $141,000 annually. Salary determinations are based on various factors, including but not limited to, relevant work experience, skills, certifications and location. CNA offers a comprehensive and competitive benefits package to help our employees – and their family members – achieve their physical, financial, emotional and social wellbeing goals.  For a detailed look at CNA’s benefits, please visit cnabenefits.com.


CNA utilizes AI-enabled technology during the recruiting process. For more information, please visit our careers page.


CNA is committed to providing reasonable accommodations to qualified individuals with disabilities in the recruitment process. To request an accommodation, please contact [email protected]

Ready to apply to CNA?
Apply to CNA

How this Software Engineer salary compares

This role pays $106,500/yr — below the typical range for Software Engineer roles.

$103,950 median $158,500 $220,150

Typical range $117,500–$160,750/yr, from 10 comparable Software Engineer listings on JobsRadar (pay annualized to USD). See Software Engineer salary insights →

About CNA

At CNA, we are focused on success, individually and collectively. We pride ourselves on promoting a culture that challenges and engages people. We strive to connect people, departments and business areas, to function as a team, and to serve our customers and communities with professionalism and respect. Our dedication to employee engagement, continuous learning and the open exchange of ideas is the cornerstone of our business. These ideals, combined with our focus on the customer, enable us to explore new market opportunities and build on our success. Our values, culture and financial strength are what differentiates us from other employers and make CNA the place you want to work.

See all jobs at CNA →

Similar jobs

Chime Financial, Inc
Senior Staff / Staff Software Engineer, Trust & Safety
Chime Financial, Inc
⚡ Apply early Chicago, IL, USA; San Francisc... Hybrid $223,000–$373,000
● New 👁 Seen ✓ Applied 1w ago
Chime Financial, Inc
Senior Software Engineer, Trust & Safety
Chime Financial, Inc
⚡ Apply early Chicago, IL, USA; San Francisc... Hybrid $164,000–$259,000
● New 👁 Seen ✓ Applied 1w ago
Chime Financial, Inc
Software Engineer, Trust & Safety
Chime Financial, Inc
⚡ Apply early Chicago, IL, USA; San Francisc... Hybrid $117,000–$184,000
● New 👁 Seen ✓ Applied 1w ago
CR
Machine Learning Software Engineer 1
Crowe
⚡ Apply early Chicago IL USA Onsite $62,000–$100,000
● New 👁 Seen ✓ Applied 2w ago
project44
Senior Software Engineer
project44
⚡ Apply early Chicago Hybrid
● New 👁 Seen ✓ Applied 4w ago
project44
Senior Software Engineer - DevOps/SRE
project44
⚡ Apply early Chicago Hybrid $130,000–$190,000
● New 👁 Seen ✓ Applied 4w ago
CN
Senior Software Engineer - Guidewire Developer
CNA
⚡ Apply early Chicago, IL, USA Onsite $72,000–$141,000
● New 👁 Seen ✓ Applied 1mo ago
FactSet
Sr. Software Engineer (C++, CI/CD, Data Structures, Algorithms, OOD) – Hybrid
FactSet
⚡ Apply early Chicago, IL, USA Onsite
● New 👁 Seen ✓ Applied 2mos ago
Light & Wonder
Senior Advanced Software Engineer - Rendering
Light & Wonder
⚡ Apply early Chicago, IL Hybrid $150,000–$172,000
● New 👁 Seen ✓ Applied 2mos ago

Sign up for suggestions tailored to the jobs you open and the searches you save.

More jobs at CNA

See all jobs at CNA →

Apply now
🤖

Whoa — hold up

JobsRadar was built for real people having a rough time in their job search — not for automated requests. You're clicking way too fast and you're now temporarily blocked.

Come back later. If you're genuinely job hunting, we've got your back — just act like a human.

Catch your next role the second it’s posted.

Create a free account and we’ll watch the boards for you — the instant a job matches your search, it lands in your inbox or Telegram. No digging, no refreshing.

Create free account

Free forever · takes 30 seconds · already have one?

Get an edge on your job hunt.

Join our Telegram channel for the stuff that helps you land the role — salary benchmarks, the weekly market pulse, and new-feature drops. No spam, just signal.

Join the channel — it's free